The short version of the Stingy Jack legend is that he was a drunkard and a conniver, who on multiple occasions had outwitted the Devil who had come to take his soul. When he finally did die, Heaven rejected him due to his sinful ways, and due to his one-upping of the Devil, Old Scratch prevented him from even being able to enter Hades.

As he walked away from Hell, Jack nabbed an ember from one of the fires, and he placed it in a hollowed-out turnip which lit his way as he navigated the netherworld in-between this world and the hereafter.

This made him now known as "Jack of the Lantern", otherwise abbreviated to "Jack o' lantern".

Pumpkins vs. Turnips

So if the original tale (and the original carved effigies) were turnips, how did jack o'lanterns come to be associated with pumpkins?

Most likely, when Irish immigrants came to America in the 1800s they brought their traditions with them and found the pumpkin — native to North America — a far superior food item for hollowing out and carving than the turnip.

Will o' the Wisp

"The term jack-o'-lantern was originally used to describe the visual phenomenon ignis fatuus(literally, "foolish fire") known as a will-o'-the-wisp in English folklore. Used especially in East England, its earliest known use dates to the 1660s.

The term "will-o'-the-wisp" uses "wisp" (a bundle of sticks or paper sometimes used as a torch) and the proper name "Will": thus, "Will-of-the-torch." The term jack-o'-lantern is of the same construction: "Jack of [the] lantern.""—via Wikipedia

It seems the legend was built around the experiences of these spooky bog lights, and the jack o' lantern somehow became a talisman or symbol of this story. I couldn't find any information as to whether the ignis fatuus has any specific association with Autumn or October.

However, it seems that the Celtic festival of Samhain (which we now know as Halloween) was seen as a time when supernatural beings (the Aos Sí), and the souls of the dead, roamed the earth. Perhaps these ghostly lights were perceived as the lanterns of these lost souls.

The Aos Si (literally, "people of the mounds") were also known as the "Fairy Folk", who lived in an invisible parallel universe that coexists with the one we inhabit. Samhain/Halloween was a time where the separating boundary between these two existences somehow became less restrictive…

I suspect the experiences of the ignis fatuus tended to occur around October, thus drawing an association in the mounds of the ancient Celts.

Stingy Jacks: the patch

So there's the background to why the pumpkin patch in this set was named the "Stingy Jacks".

When the concept for the Halloween-themed, biker-style patch concept came to me, the club name "Stingy Jacks" leapt to mind (with Skeleton Crew a close second).

It sounded somewhat like a biker gang (I mean, motorcycle club) name, the lore behind the name was a geeky Halloween connection, and it just sounds cool!

The initial sketch for the Stingy Jacks patch pretty much became the final art. It was the first sketch I made, and the style in which I did the dark shading so the glowing face really stood out was proof-of-concept for me that this set could work with just the limited palette of orange, black and white.

"Stingy Jacks" initial color concept sketch

I knew regardless of the rest of the set, all of them needed to used a limited color palette of black, orange and white.